ESUBERAPROST POTASSIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H29O5.K
Molecular Weight	436.5824
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[K+].[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)[C@@H](C)CC#CC)[C@@]1([H])C3=C(O2)C(CCCC([O-])=O)=CC=C3

InChI

InChIKey=RSTLTBUTQXBUMK-ZTWNIFTGSA-M

InChI=1S/C24H30O5.K/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28;/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28);/q;+1/p-1/b13-12+;/t15-,17-,19+,20+,21-,23-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	K
Molecular Weight	39.0983
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H29O5
Molecular Weight	397.4841
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800040766 | https://pulmonaryhypertensionnews.com/2019/04/11/united-therapeutics-ends-clinical-development-of-esuberaprost-as-add-on-therapy-for-pah/

Esuberaprost (314d) is an active enantiomer of beraprost, a prostacyclin analog. The pharmacologic action of esuberaprost is mediated by specifically binding to PGI2 receptors in smooth muscle cells (the blood vessel’s endothelium) and platelets. Upon binding, the compound widened blood vessels, preventing the formation of blood clots, and lowering blood pressure in the lungs. As a result, it was expected to improve the symptoms of pulmonary arterial hypertension. United Therapeutics announced it has ended its Phase 3 BEAT trial testing esuberaprost as an add-on therapy to its product Tyvaso (inhaled treprostinil) for clinically symptomatic patients with pulmonary arterial hypertension (PAH). According to a company press release, the study failed to reach its main endpoint of delaying the time to first clinical worsening events.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostacyclin receptor 9 Target ID: P43119 Gene ID: 5739.0 Gene Symbol: PTGIR Target Organism: Homo sapiens (Human) Sources: https://www.covance.com/content/dam/covance/assetLibrary/posters/PatelACCP16-BPS-314d-MR-Warfarin.pdf	Binding Agent 1064

PubMed

Title	Date	PubMed

Sample Use Guides

In Vivo Use Guide

Phase III study: 15 μg tablets for oral, 1 or 2 tablets four times daily (QID) administration

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:20:47 GMT 2023` Edited by `admin` on `Sat Dec 16 14:20:47 GMT 2023`
Record UNII	D49PS93IMN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESUBERAPROST POTASSIUM

Official Name

English

ESUBERAPROST POTASSIUM [USAN]

Common Name

English

(+)-POTASSIUM 4-((1R,2R,3AS,8BS)-2-HYDROXY-1-((1E,3S,4S)-3-HYDROXY-4-METHYL-OCT-1-EN-6-YN-1-YL)-2,3,3A,8B-TETRAHYDRO-1H-CYCLOPENTA(B)(1)BENZOFURAN-5-YL)BUTANOATE

Systematic Name

English

1H-CYCLOPENTA(B)BENZOFURAN-5-BUTANOIC ACID, 2,3,3A,8B-TETRAHYDRO-2-HYDROXY-1-((1E,3S,4S)-3-HYDROXY-4-METHYL-1-OCTEN-6-YN-1-YL)-, POTASSIUM SALT (1:1), (1R,2R,3AS,8BS)-

Systematic Name

English

Code System Code Type Description

SMS_ID

300000011142